Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

Anders Lindhardt Hansen and Troels Skrydstrup*

*Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark, Email: tschem.au.dk

A. L. Hansen, T. Skydstrup, J. Org. Chem., 2005, 70, 5997-6003.

DOI: 10.1021/jo050669u

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Abstract

Highly regioselective and efficient Heck reactions of aryl triflates with N-acyl-N-vinylamines were achieved using Pd₂(dba)₃, dppf, and diethylisopropylamine in dioxane. The coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketones or in situ hydrogenation in the presence of (Ph₃P)₃RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of benzylic amines.

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Key Words

Heck Reaction, Benzylic Amines, Aryl Ketones

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ID: J42-Y2005-880